


Day in the Life

by ContraryBee



Category: Supernatural
Genre: Dean in Panties, Dry Humping, M/M, Panties, Size Kink, Wall Sex, Wincest - Freeform
Language: English
Status: Completed
Published: 2016-11-21
Updated: 2016-11-21
Packaged: 2018-09-01 06:33:14
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,564
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8612983
Author URL: https://archiveofourown.org/users/ContraryBee/pseuds/ContraryBee
Summary: Sam discovers Dean's small kink, and catches his brother before he can flee.





	

Dean Winchester will never admit out loud, to anyone but himself, that he likes wearing ladies underwear. Just something about wearing a slim piece of light blue flimsy material under his jeans as he goes about his day fills him with an odd kind of happiness, almost smug, and exciting at the same time. What Dean especially liked, was that Sam didn’t know.

That’s hard to do, when you live out of another man’s pockets as they have done their entire lives. Especially after their relationship took that one last, damning jump, hiding a pretty handful of sweetly colored panties from his brother was harder than Dean thought it should be. He didn’t have anything that had color to it, not a damn shirt, a coat, only those scraps of soft fabric, pink, green, baby blue. He had to wrap them up in a black sack and slip it into the ripped lining of his bag. But it gave him such an incredible feeling, standing next to Sam and twitching his hips just enough to feel the satin, or silk, or lace, slide. Sam had no idea, and Dean would have loved to keep it that way.

But living in the bunker, Dean’s guard has fallen. Dean’s guard was non-existent, they hadn’t hunted anything really dangerous for months and Dean has found himself liking it. So when Sam gets home early, and the only things Dean is wearing his robe and a soft pair of green panties, with little pink bows on the sides, Dean doesn’t know what to do.

Obviously he’s naked under the robe, as Sam raises an eyebrow at him when he notices. But the robe is…fairly short. And thin. And the little bows are a little bit obvious when he moves in a particular way. So Dean stays as still as he possibly can on the couch, as Sam grabs them both a beer and collapses beside him.

He managed about an hour of casual conversation, before his nerves gathered enough to get him to stand up. And of course, the robe gaped at just the right moment for Sam to catch a glimpse of baby soft green. Sam froze, Dean froze, the air between them stretched on, waiting.

“Dean…” Sam’s voice was strangled, “are you wearing…panties?”

“I don’t know what you’re talking about, Sam, you’re seeing things.” Dean replied, his heart in his throat. He managed to get to the door before Sam could move. But the thing about Sam is that he has really long ass legs. Three strides caught him up to Dean, and another shoved them both into the wall. Dean gasped, cursing when all of a sudden his escape plan was halted by an immovable body.

Large paws stroked down into Dean’s robe, investigating. Dean could feel his neck and ears burning with shame and heat as he struggled against the stone body behind him. Their previous sexual encounters had never really had one brother more aggressive than the other; this strong, growly Sammy was a Sam Dean had only ever spied on before. That was also something Dean would never admit to himself, he liked how big Sammy was, and how so utterly strong.

“Sam!” He snapped, trying to be angry, “what are you doing – get your mitts offa me!”

“Dean.” Sam’s voice was a growling exhale, shocked and immensely aroused when his hands found Dean’s hips clad in satiny green cloth. His huge fingers rolled and pressed, massaging the fabric, and the skin underneath. Dean shuddered and his breathing quickened until he was panting into the wall, eyes squeezed shut.

“Do you do this often? Wear pretty panties beneath your clothes?” Sam grunted into his ear, pressing harder, pulling the robe aside.

“Yeah, what of it?” Dean tried to answer sarcastically, but Sam clenched his fingers and it turned into a bit of a squeak, a manly squeak, of course. Sam’s lips scrawled a hot line across his shoulder and neck, leaving behind a wet trail of spit. One of Sam’s huge hands spread across Dean’s rapidly rising cock, trapped in its satin prison, and the other dragged up his stomach to pull and yank the robe off his shoulders to pool at his feet.

Suddenly exposed, Dean whined and moved into Sam’s hold on him, cock hard in his little brother’s grip. Rubbing up against the small of his back was Sam’s own hardness, hot, and huge as his brother’s hips rolled against him. Sam held him tight to the large expanse of his chest, thrusting them both into the wall with powerful moves of his hips. It was like time had stopped, they didn’t care they stood awkwardly in the living room of the bunker, facing a blank wall.

“Pretty Dean, they match your eyes.” Sam pants, mouth latching onto the back of his neck.

“S-shut up, you ass.” Dean growled. Sam’s fingers that weren’t stroking and touching Dean’s cock pinched at a nipple for a second, before crawling up to wrap around his neck, tipping his head back onto Sam’s shoulder behind him. Dean felt like he was curved into a big C, one hand on his cock bending him back to rub his cheeks against Sam, another holding his neck tight so he could only blearily stare at the ceiling and gasp.

“No, Dean, s’hot.” Sam’s hot fucking mouth bit along his jaw line, eventually reaching Dean’s mouth and licking inside. Kissing, they moved together, crushing Sam’s hand between Dean’s cock and the wall, crushing Dean, cutting off his breath.

“Fuck, Sam, I, I can’t...” Dean panted into his brother’s mouth, wet lips sliding together lewdly. He was already leaking into the stretched panties, seeping through and wetting Sam’s hand. Sam made a noise, a combination of a growl and a whimper, shoving harder into Dean.

Knees shaking and feeling weak, Dean writhed in his brother’s grip.

“How long?” Sam asks, “how long have you been wearing pretty girls’ clothes?”

“Since, god, since high school.” Dean groans, eyesight wavering as he draws so close to orgasm he trembled with it.

Sam jerks and swears, coming in his jeans. Dean cries out as Sam’s hand tightened cruelly on his cock, loving how it kicked his pleasure up another level. Sam bared his teeth against the soft skin under Dean’s ear, heaving through his orgasm. Dean felt himself struggle to breathe for a split second as Sam leaned his weight on him, coming with a wrecked cry in that instant.

“Fucking, god, so hot Dean, look at you, wetting your panties.” Sam grunted, head craning down to watch as Dean’s come soaked into the fabric. Those giant fingers of his massaged and pressed into Dean’s skin, drawing moans out of the shuddering mess in his grasp. Knees weakening, Dean fell back into Sam, whimpering a little from the force of his orgasm.

They slumped against the wall, panting. Dean felt a little ridiculous, face pressed into the doorframe with Sam‘s pointy nose huffing hot air into his ear. But the orgasm he just had put him in the best of moods. So, he squirmed a little to feel and enjoy the wetness of the panties, and the hard planes of Sam’s body behind him.

Sam groaned against his skin, twitching. “Stop moving, Dean.” He complained, falling away from Dean to stumble and fall onto the couch. His pants were open, cock a line beneath his boxers, head peeking just a little from the waistband.  God, he was attractive.

Dean, deciding to go ahead with his instincts, stripped himself out of his panties and stretched out naked on the couch beside Sam, feeling incredibly attractive for some reason. There was a sort of erotic thrill to being bare while Sam was fully clothed just feet away. He felt something like a whore, but better…maybe a courtesan, or a mistress. How ridiculous was that. Sam’s eyes devoured him, and despite his recent orgasm, Dean felt himself responding.

“High School, Dean?” Sam rasped, licking his lips.

Dean gave a happy grumble, loving how free his body felt; naked and sweaty. It sent an electric thrill through him, made him wet his lips. Sex was awesome.

“Rhonda Hurley,” Dena gave a slow smirk, eyes growing distant as he remembered that hurricane of a girl, “made me put on her panties while I fucked her. This little tiny pink pair, see-through and lacy. I loved it.” Sam’s breath audibly punched out of him, and one of his large hands came to rest on Dean’s knee.  

“And hey, took you this long to realize. What else do you think you’ve missed?” Dean’s grin was shark-like, and it ignited something in Sam. The bigger man crawled up the length of Dean’s gloriously bare body, not touching, just hovering, until their mouths came up even. Sam smiled through his lust, when Dean squirmed a bit to try and reach him, to bring their lips together.

“If you’re going to be that way about things,” Sam said dangerously, “I have some things that I want you to wear. Don’t you worry Dean.” Sam finally brought their mouths together, the only place that touched between them, Sam clothed, Dean unclothed, cocks coming back to life.

“What have you got for me Sammy?” Dean whispered, panting hotly, “Something as pretty as those panties?”

Sam grinned a dark grin, “Prettier.”

**Author's Note:**

> Man, I love domestic wincest. And bottom Dean. Gruff, growly, rude Dean with a kink for being the smaller brother.


End file.
